Five crucial questions to ask your love interest

By Dave Singleton

Who can remember a litany of what to say and do — or not do — on a date? That’s exhausting! If rule #1 of dating is “be yourself,” perhaps rule #2 should be: “Create a simple game plan for conversation that helps you discover the real person who’s hiding behind the chatty façade on your date.” This is way more important than choosing where to have drinks or which movie to see, because you want to try and genuinely connect with each other. Finding out what her favorite drink is or where he went to graduate school is useful background info to have, but what do you really know about someone after asking those kinds of questions? Not much!

Nor do you want to engage in conversational dead ends by trading bits of information followed by silence (until one of you picks up the small-talk baton and starts running with it again). That’s not two people forming a connection; rather, it’s more like trading mutual monologues with each other. You want to find out fast if your date has potential. You want to stop repeating past mistakes and keep your eyes open for clues that might reveal whether Mr./Ms. Maybe is a keeper — or just another cast-off. But the trick is not to come off as being too heavy-handed, like you’re leading an interrogation squad; after all, it’s a date, not CSI: Romantic Shakedown.

Recently, I spoke to men and women who’ve mastered the art of investigative finesse on their love interests. They each became tired of swimming in the shallow end of the conversational pool and subsequently came up with at least one question that’s guaranteed to get either a date or longer-term partner to open up and move into deeper, more substantial waters. So before your next discussion ends with you drowning in the banality of whatever you both had for lunch today (and without an inkling of what really makes the other person tick), consider asking one of the five quintessential queries listed below:

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I am a:

Seeking a:

Near:

Crucial Question #1: “What are you really passionate about right now?”
“I usually lean in, look him in the eye and say, ‘So, tell me...what are you really passionate about?’” says Washington resident Heather, 37. “Sometimes, my date responds with another question (‘what do you mean?’). I reply by saying that I’m genuinely interested in whatever excites him most in life. What does he love doing more than anything else? Sometimes this question makes my dates uncomfortable, and they shift around in their seats and say that they don’t really know what to tell me. Or they respond by telling me that they like ‘the normal stuff — work, hanging out with friends, etc.’ I look for the guy who brightens up at the question and starts to tell me all about whatever it is that he’s into right now. To me, it really doesn’t matter what makes him happy — it’s more important to me to know that there is something in this world that he is really engaged in and feels passionately about. I find that passion really attractive.”

Crucial Question #2: “If you could go back and do one thing differently in your life, what would it be?”
“After all the dating I’ve done, I definitely developed a #1 question for my dates,” says California native Jennifer, 34. “If they could go back and redo one thing over in life, what would it be? It never fails! I hear about something that didn’t work out and then about how this person’s spent time trying to fix it — or just moved on and learned from it instead. This question never elicits a negative response, and I always offer to share mine with my date. It makes men think without being intimidating, and it also makes them realize that I’m not a run-of-the-mill woman who just wants to talk about what’s on the menu at dinner.”

Crucial Question #3: “Which three people — living or dead — would you invite to dinner, and why?”
“I ask my dates which three people (living or dead) they’d invite to dinner, and what kind of meal they would make,” says Steve, 34, of Chicago, IL. “At first, it seems like an easy, fun question — which is why I like asking it. It’s not awkward and doesn’t pry or push for too much information, which I never do on a first date. But when you ask something like this, you can see the wheels in the other person’s mind begin to spin and prioritize the people invited to join in this fantasy dinner. You find out a lot about someone’s heroes, who inspires this person and why, and also usually something about the topics your date cares about most in life. One woman answered with the names of three religious figures, which is how I discovered how important her faith was to her. Another answered with a list of vapid pop culture celebrities, which was the first indication that we didn’t share that much in common — and I soon found out there were more indicators, so this was a good heads-up early on. One woman mentioned her parents, and I immediately got a sense of how important her family was to her. It never fails to let me in on important information I’d never get by just engaging in typical date-night banter.”

Crucial Question #4: “What’s the one thing that surprises you about dating now vs. how it was 10 years ago?”
“I like to get a sense of my date’s perspective and history,” says North Carolina native Margaret, 45. “Since the men I date are older and divorced, like me (or maybe they are just out of a long-term relationship, widowed, or have just been single all these years), this question usually gives them pause. When they finally answer me, I’m able to get a sense of whether they’re cynical or hopeful, whether they’ve learned something distinct and valuable about love from their previous experiences, or just see their prior relationships as being all blended together somehow. I also get an idea of what they’re looking for and what they’d like to bring into a potential new relationship. I can then share my own experiences, and on a few occasions, I’ve found that this is an incredibly bonding discussion to have with my date.”

Crucial Question #5: “What did you do last weekend?”
“I like finding out concrete things about the women I date,” says Maryland resident Alex, 36. “So I don’t ask theoretical questions about quantum physics or what you’d take with you if a house fire broke out. I ask what my date did last weekend and like getting into the details with her, because those details usually lead to even more details… and the truth is, compatibility is all about those details. I like focusing on weekends, which is usually when people have the most control over their personal time, so how they choose to use it is quite revealing. Maybe she’ll tell me that she spent it with friends, and that it’s her favorite way to spend a weekend. OK, then, she’s really social; I get it. Or she’ll tell me that she went skiing and that she loves taking active weekend trips. That would work for me, since I’m a super-active guy. Or maybe she spent it reading with her cats because she needs lots of downtime. I’m extroverted and always on the go, so I like a woman who enjoys constantly being on the go, too. People can tell you what you want to hear if you ask them theoretical questions. But if you ask them about their actual experiences, you’ll find out what they’re really all about much, much quicker.”

Dave Singleton, an award-winning writer and columnist for Match.com since 2003, is the author of two books on dating and relationships. Visit hiswebsite, follow him onTwitter, oremail him.